2R-tert-butoxycarbonylamino-3-[4-(2R-tert-butoxycarbonylamino-2-methoxycarbonyl-ethylsulfanyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-ylsulfanyl]-propionic acid methyl ester | 1266665-92-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2R-tert-butoxycarbonylamino-3-[4-(2R-tert-butoxycarbonylamino-2-methoxycarbonyl-ethylsulfanyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-ylsulfanyl]-propionic acid methyl ester
• 英文别名: dimethyl 3,3'-((2,5-dioxo-2,5-dihydro-1H-pyrrole-3,4-diyl)bis(sulfanediyl))(2R,2'R)-bis(2-((tert-butoxycarbonyl)amino)propanoate)；2,3-Di-(N-Boc-Cys-OMe)-maleimide；methyl (2R)-3-[4-[(2R)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]sulfanyl-2,5-dioxopyrrol-3-yl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1266665-92-2
• 化学式: C₂₂H₃₃N₃O₁₀S₂
• 分子量: 563.65
• InChiKey: NUKNWGAFWGPVCM-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  226
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  苯乙烯 、 2R-tert-butoxycarbonylamino-3-[4-(2R-tert-butoxycarbonylamino-2-methoxycarbonyl-ethylsulfanyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-ylsulfanyl]-propionic acid methyl ester 以 乙腈 为溶剂， 反应 0.5h， 以60%的产率得到2-aza-4,7-di((2R)-tertbutoxycarbonylamino-3-sulfanyl-propionic acid methyl ester)-5-phenylbicyclo[3.2.0]heptan-1,3-dione
  参考文献：
  名称：

  [2 + 2] Photocycloadditions of thiomaleimides

  摘要：

  溴马来酰亚胺与硫醇（包括半胱氨酸）加成生成的硫代马来酰亚胺可发生高效的 [2â+â2] 光环加成反应。

  DOI：

  10.1039/c2cc31673k
• 作为产物：
  描述：

  3,4-二溴-1H-吡咯-2,5-二酮 、 N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以100%的产率得到2R-tert-butoxycarbonylamino-3-[4-(2R-tert-butoxycarbonylamino-2-methoxycarbonyl-ethylsulfanyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-ylsulfanyl]-propionic acid methyl ester
  参考文献：
  名称：

  [2 + 2] Photocycloadditions of thiomaleimides

  摘要：

  溴马来酰亚胺与硫醇（包括半胱氨酸）加成生成的硫代马来酰亚胺可发生高效的 [2â+â2] 光环加成反应。

  DOI：

  10.1039/c2cc31673k

文献信息

• Reversible covalent linkage of functional molecules
  申请人：Smith Mark

  公开号：US09295729B2

  公开（公告）日：2016-03-29

  The present invention relates to the use of a compound containing a moiety of formula (I) as a reagent for linking a compound of formula R1—H which comprises a first functional moiety of formula F1 to a second functional moiety of formula F2 wherein X, X′, Y, R1, F1 and F2 are as defined herein. The present invention also provides related processes and products. The present invention is useful for creating functional conjugate compounds, and specifically conjugates in which at least one of the constituent molecules carries a thiol group.

  本发明涉及使用含有式(I)的基团的化合物作为将具有式F1的第一功能基团的化合物R1-H与具有式F2的第二功能基团连接的试剂 其中X、X'、Y、R1、F1和F2如本文所定义。本发明还提供相关的工艺和产品。本发明适用于制备功能共轭化合物，特别是至少一种组分分子携带硫醇基团的共轭物。
• A Light‐Induced Decarboxylative‐Elimination of Substituted Maleimides as a Strategy Towards Triggered Photorelease
  作者：Roshni Malde、Daniel A. Richards、Luigia Salerno、Yanbo Zhao、Kersti Karu、Vijay Chudasama、James R. Baker

  DOI：10.1002/ejoc.202201372

  日期：2023.5.12

  Herein we report on photodecarboxylations of various substituted maleimides, resulting in an elimination reaction. Furthermore, we establish facile wavelength tunability through modulation of the maleimide double bond substituents. We envisage that these versatile reagents, which are readily constructed and diversified by nucleophilic substitution reactions on bromomaleimides, will offer new opportunities for triggered photorelease.

  摘要我们在此报告了各种取代马来酰亚胺的光脱羧反应，并由此产生了消除反应。此外，我们还通过调节马来酰亚胺双键取代基建立了简便的波长可调性。我们设想，通过对溴马来酰亚胺的亲核取代反应，这些多用途试剂很容易构建并实现多样化，这将为触发式光释放提供新的机遇。
• Conjugation-Induced Fluorescent Labeling of Proteins and Polymers Using Dithiomaleimides
  作者：Mathew P. Robin、Paul Wilson、Anne B. Mabire、Jenny K. Kiviaho、Jeffery E. Raymond、David M. Haddleton、Rachel K. O’Reilly

  DOI：10.1021/ja3105494

  日期：2013.2.27

  Dithiomaleimides (DTMs) with alkyl substituents are shown to be a novel class of highly emissive fluorophores. Variable solubility and further functionalization can easily be tailored through the choice of N and S substituents. Inclusion of a DTM unit into a ROP/RAFT initiator or insertion into the disulfide bond of salmon calcitonin (sCT) demonstrates the utility for fluorescent labeling of polymers and proteins. Simultaneous PEGylation and fluorescent labeling of sCT is also demonstrated, using the DTM unit as both a linker and a fluorophore. It is anticipated that DTMs will offer an attractive alternative to commonly used bulky, planar fluorophores.
• [2 + 2] Photocycloadditions of thiomaleimides
  作者：Lauren M. Tedaldi、Abil E. Aliev、James R. Baker

  DOI：10.1039/c2cc31673k

  日期：——

  Thiomaleimides, generated by the addition of bromomaleimides to thiols including cysteine, undergo highly efficient [2 + 2] photocycloadditions.

  溴马来酰亚胺与硫醇（包括半胱氨酸）加成生成的硫代马来酰亚胺可发生高效的 [2â+â2] 光环加成反应。